If there is one trait every executive asks for in an EA, it is proactivity. The ability to anticipate needs, solve problems before they appear, and stay several steps ahead. A proactive EA can change your life in ways you feel every day.
And yes, proactivity should originate from the EA. It is part mindset, part curiosity, and part pattern recognition. But there is another side to this that leaders rarely talk about.
Sometimes the lack of proactivity is not a capability gap. Sometimes the EA is ready to be proactive, but the environment makes it harder than it needs to be. The most proactive EAs thrive when they have the right visibility, context, and trust.
The strongest partnerships create those conditions together.
Proactivity is not magic. It is the outcome of clarity.
Executives are often surprised to learn that proactivity is built long before action happens. It begins with a shared understanding of your world and a clear picture of what matters most to you.
EAs cannot read minds. They read patterns. They read context. They read habits. And if they do not have access to those things, their proactivity has a ceiling.
Here are the biggest reasons EAs hold back, even when they do not want to:
- They do not know your priorities.
If your EA is unsure what matters most this week or this quarter, they will struggle to anticipate where you need attention or support. - They do not want to overstep.
When expectations around ownership or decision-making are unclear, even a talented EA will hesitate. - They do not have enough context.
If they are kept out of key conversations, meetings, emails, or documents, they can only react to what they see. - They feel rushed, shut down, or corrected too often.
Proactive behavior grows in environments where ideas are welcomed and risks are safe.
None of these blockers reflect an EA’s actual potential. They reflect the partnership conditions around them.
How you can help your EA become more proactive
A proactive EA is not created by hoping for it. It is created by building the conditions where proactivity is possible.
Here are practical ways to do that:
Share the why, not just the what.
When your EA understands your goals and pressures, they can anticipate the next three steps instead of the next task.
Invite them into your world.
Loop them into meetings, forward important emails, talk them through decisions, and share what keeps you up at night. Context gives them a runway.
Encourage questions.
Every great EA asks thoughtful questions. If they stop asking, it usually means they feel shut down.
Be clear about decision rights.
Say out loud what they can take off your plate completely, what needs your approval, and what you want to stay deeply involved in.
Respond with curiosity when they take initiative.
Even if something is not perfect, the moment your EA reaches forward is the moment to strengthen that behavior.
Hold a monthly alignment conversation.
Ask what feels unclear, what they would like more ownership over, and where they see opportunities to support you better.
What proactivity feels like in a great partnership
A proactive EA partnership is not just about tasks happening on time. It is about how you feel in your work and in your life. It creates a sense of ease that you can feel in your shoulders, your breathing, your focus, and your overall energy.
Here is what it feels like:
You start your day without bracing for impact.
You are not walking into a surprise or a fire drill. You feel settled instead of scattered.
Your brain feels quieter.
You are not holding a hundred mental tabs open. The clutter is gone, and you can actually think.
You feel caught, not dropped.
Even if you forget something, your EA has already caught it and moved it forward. You feel held rather than behind.
Your time feels like it belongs to you again.
Your EA protects it with intention. You feel less reactive and more in control.
You stop apologizing for being late, overwhelmed, or unreachable.
Your EA is keeping your world in motion with you and for you.
You experience momentum instead of friction.
Things you used to push uphill now flow because someone else is clearing the path.
Your work stops feeling like survival mode.
You can finally focus on what matters instead of triaging what is on fire.You breathe deeper, and you breathe differently.
You feel supported before you even ask. You feel like your work has space again.
Final thought
If you want more proactivity from your EA, start by asking yourself:
Have I set the conditions where proactivity is possible?
Because when an EA has visibility, context, encouragement, and clear authority, their initiative has room to grow. Their ideas get bolder. Their anticipation sharpens. And the partnership becomes the kind that changes not just how you work, but how you feel in your work.
Reflection prompt
What is one thing you can give your EA this week that would help them anticipate your needs more easily?
